Anthracene dye and process of making same.



UNITED .STATES PATET. OFFICE.

REN BOHN, OI MANNHEIM, GERMANY, ASSIGNOR TO BADISOHE ANILIN & SODA FABRIK,

0F LUDWIGSHAFEN-ON-THE RIIINE,l GERMANY, A CORPORATI'DN.

AIil'TI-IRAGENE DYE AND PROCESS OF MAKING SAME.

No.l 868,399.

Application man June 18.

that by treating hydroxyaiithraquinones, or derivatives Specication of Letters Patent.

1907. Serial No. 379,680.'

Patented ont. 15, 1907.

thereof, with formaldehyde and with a salt ci sulfurous acid in the presence oi alkali, new. compounds can-he obtained which arc easily soluble in water and so differ from the hydroxyanthraquinones. The new compounds can be used as coloring matters, or as materials for the. production ol other compounds.

l The following table gives the properties of some of the new coloring matters obtainable according to my invention.

Solution in- I Shade on Colormg mutter rm Dilutc caustic i Fone sulfuric Diluie sulfuric chromu'mor l mu" soda. i l acid. i acid. danced bu Anthracenc blue WR H hlish r l....Y Illm` Ylolet .E Red Blue. Cyelamin lied \'iolet. 1 Blue. Pentncyanin R )ivd-violet. f Blue. 1.2.3.5.7-pentnoxyfanthraquinone Orange-red Orange l Brown. Anthrachryson... vn. Holl-brown Ilrown Yellow-green., Red-brown. Alizarinbordeaux \'iolcl-llul i.. Red-violet... i Brown-rcd Violet-blue.

The following is an example of how my invention can be performed, but it is not confined to ihisvex-.nnplc4 The 4parts are by weight. l l

'lo .one hundred (,100) parts' oi-u- Jeen (10) per ccnl. paste ol the hexahydroiryaut-hraqninone known in commerce as anthraccnc bluell/'It-extra, add n'hhstirring well, one hundred (100) parts of a thirty (lill) per cont..sodinm sullite solution and sixty (6U) parts oi l' a twenty-four per" cent. causie sod-.t solution. Then allow ironriivc (5),- to sin4 (6), parts ol a thirty (30) per cent1 formaldehyde solution to [low into the' n'iixture, and heat for iroln three (3), lo ivc (5), hours at a temperature of from ninety (90) to one hundred (100), degrees centigrade. When the mixture is cool, acidity it bymean's of about one hundred and llieen (U5) In thisexnple, the quantity of sulllc and of alkali said, consists of a dark brown powder which is easily employed can be considerably varied.

The compound, or coloring matter, ol'ltaiucd as aforesoluble in water yielding a bluish rcdsolulon, and it can be precipitated from the solution by .the addition of common sal l'.,orol sodiulnsulate. yiclds'a blur` solution in dilute caustic. soda-solution, aV .violet solution in In -a similar manner, other hydroxyanthraquinones can lle Irealcd with formaldehyde and-a sullite in the presence ol' alkali, such fol-'instance as hexaoyanin l lhcxahydroxyanl hraquinone), '.ilizarincyanin lt (penta- :hy |r:xyanlhraquimme), and Alix-erin Bordeaux (li-lrahy(lroxyan'lhraquinone).

l. 'l'he process ol' producing." coloring: matters of the :ullhrnccnc V .sci-les lu' lrealing a liydroxyanthraqu[none body willi iornnildchyde and wilh n salt of sulfulous ncid in iho presence ol' alkali.

L. 'lhe process ol |umlucin; r coloriug`matters of the antilla-icone series' h r treating hexnhydroxyanthraquInoue with' l'ornulldehydc and with .a salt ot' sulfurous acid in the presence or' alkali. ,I

which cnn hc obtained by treatingr a hydroxyanihraquinone hmly "lh l`ornuildeh \'de and with n Snli: of sulfurous acid in Ihe presence ol' alkali, which coloring nutttelsyleld blu lo red-brown soluiiorzsl in dilute caustic sulla. orange-red lo violet solutions i( concentrated sulfuric ncd, red to dye cotton mordani'echvlth chromium com-pounds yielding` from violet-blue to red-brown shades.

obialnahlc by trealim: liexnl\ vdrox \'nntln'uuninune with -fornnldchyde und `wilh u snit' o( .snll'urous ucidNln. the 1n-esenec,ol alkali.' which coloring,r mntteivylcl'ds bluish red solutionl in wall-r. blue solutions in dilute caustic soda, rlolcr solulious in conecntrnied sulfuric ucidlund 'roti solullons in dilulc sulfuric acid, und which 'dye cotlou-morilanlml'with cl'n'ominm compounds yielding blue shades.

In lcslhnonyl n'hcrcol' I have lhe. presence ol' two sultscrihhn;- witnesses.

, mann noun.

Witnesses .l'. Al.i.c. [.Loru;

FluNns'rl\.' linnulino'r,

:L As new arlicles of nmnu'facl'ure the coloring matters lah red lo. yellowlsh'hi'own solutions` in water, violet-blue yellowish green -solui ms in dilute sulfuric ncl-d and which hereunto set my hand in 4. As n new nrllcle of nmnufnclure the'coloringmatter` I` 

